1,1'-Carbonyldiimidazole → N-Methoxy-N-methyl-1H-indazole-3-carboxamide

HRID 218458

반응식

HRID 218458 반응식
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1)(O)=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:26][NH:27][O:28][CH3:29]>CN(C=O)C>[CH3:29][O:28][N:27]([CH3:26])[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1)=[O:2]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 78250Indazole-3-carboxylic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

생성물 1

HCID 16036867N-Methoxy-N-methyl-1H-indazole-3-carboxamide수율 81.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

3-Carboxyindazole (10 g, 61.7 mmol) in DMF (100 mL) was treated with carbonyldiimidazole (11 g, 67.84 mmol) at rt with gas evolution for 15 min, after which the reaction mixture was heated up to 65° C. for 2 hours. After cooling to rt, N,O-dimethylhydroxyamine-HCl (4.14 g, 67.8 mmol) was added and the mixture was heated to 65° C. overnight. The reaction was cooled, quenched with water, extracted with CH2Cl2 and washed with water. The combined organic phase was dried and concentrated to afford N-methoxy-N-methyl-1H-indazole-3-carboxamide (10.3 g, 81.4%).

후처리

  1. temperatureAfter cooling to rt
  2. temperaturethe mixture was heated to 65° C. overnight
  3. temperatureThe reaction was cooled
  4. customquenched with water
  5. extractionextracted with CH2Cl2
  6. washwashed with water
  7. customThe combined organic phase was dried
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c678d9ae3a624567bfad52efe9f10168
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198456B2

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